CA1240338A - Preparation d'acide n,n,-dicarboxymethyl- aminomethylenephosphonique - Google Patents
Preparation d'acide n,n,-dicarboxymethyl- aminomethylenephosphoniqueInfo
- Publication number
- CA1240338A CA1240338A CA000475168A CA475168A CA1240338A CA 1240338 A CA1240338 A CA 1240338A CA 000475168 A CA000475168 A CA 000475168A CA 475168 A CA475168 A CA 475168A CA 1240338 A CA1240338 A CA 1240338A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- alkali metal
- metal salt
- salt
- diacetic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims abstract description 47
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims abstract description 60
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 33
- -1 alkali metal salt Chemical class 0.000 claims abstract description 33
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 20
- 239000011707 mineral Substances 0.000 claims abstract description 20
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 239000002244 precipitate Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- 239000000413 hydrolysate Substances 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 6
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims 3
- KKHJQZVEUKJURX-UHFFFAOYSA-N 2-(carboxymethylamino)acetic acid;hydrochloride Chemical compound Cl.OC(=O)CNCC(O)=O KKHJQZVEUKJURX-UHFFFAOYSA-N 0.000 claims 2
- 239000012431 aqueous reaction media Substances 0.000 claims 2
- BSRDNMMLQYNQQD-UHFFFAOYSA-N iminodiacetonitrile Chemical compound N#CCNCC#N BSRDNMMLQYNQQD-UHFFFAOYSA-N 0.000 claims 2
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 8
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- 230000011514 reflex Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XWSGEVNYFYKXCP-UHFFFAOYSA-N 2-[carboxymethyl(methyl)amino]acetic acid Chemical compound OC(=O)CN(C)CC(O)=O XWSGEVNYFYKXCP-UHFFFAOYSA-N 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical compound OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- ILVUABTVETXVMV-UHFFFAOYSA-N hydron;bromide;iodide Chemical compound Br.I ILVUABTVETXVMV-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58403884A | 1984-02-27 | 1984-02-27 | |
| US676,749 | 1984-12-05 | ||
| US06/676,749 US4724103A (en) | 1984-02-27 | 1984-12-05 | Process for preparing N,N-diacetic acid aminomethylenephosphonic acid |
| US584,038 | 1996-01-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1240338A true CA1240338A (fr) | 1988-08-09 |
Family
ID=27078970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000475168A Expired CA1240338A (fr) | 1984-02-27 | 1985-02-26 | Preparation d'acide n,n,-dicarboxymethyl- aminomethylenephosphonique |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4724103A (fr) |
| EP (1) | EP0155926B1 (fr) |
| KR (1) | KR870001766B1 (fr) |
| AU (1) | AU568187B2 (fr) |
| BR (1) | BR8500859A (fr) |
| CA (1) | CA1240338A (fr) |
| DE (1) | DE3564688D1 (fr) |
| ES (3) | ES8606367A1 (fr) |
| GB (1) | GB2154589B (fr) |
| HU (1) | HUT39455A (fr) |
| IL (1) | IL74454A (fr) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU205944B (en) * | 1988-02-08 | 1992-07-28 | Nitrokemia Ipartelepek | Process for producing n-phosphono-methyl-imino-diacetic acid |
| HU200780B (en) * | 1988-02-08 | 1990-08-28 | Nitrokemia Ipartelepek | Process for producing n-phosphonomethyl iminodiacetic acid from double salt of iminodiacetic acid |
| US5167866A (en) * | 1989-12-15 | 1992-12-01 | W. R. Grace & Co. Conn. | Control of corrosion in aqueous systems using certain phosphonomethyl amine oxides |
| US5312972A (en) * | 1992-10-29 | 1994-05-17 | Hampshire Chemical Corp. | Conversion of hydroxymethyl-iminodiacetic acid to phosphonomethyl-iminodiacetic acid |
| GB9300641D0 (en) * | 1993-01-14 | 1993-03-03 | Zeneca Ltd | Process |
| US5312973A (en) * | 1993-03-25 | 1994-05-17 | Finchimica S.P.A. | Process for producing n-phosphono-methyl-imino-diacetic acid |
| AU699417B2 (en) * | 1995-03-14 | 1998-12-03 | Monsanto Company | Treatment of a formaldehyde-containing waste stream |
| US6365772B1 (en) | 1995-05-30 | 2002-04-02 | Hampshire Chemical Corp. | Facile synthesis of phosphonomethylglycine from phosphonomethyliminodiacetic acid |
| EP0833831B1 (fr) * | 1995-06-07 | 2002-02-13 | Monsanto Technology LLC | Procede d'elaboration d'acide n-phosphonomethyliminodiacetique |
| US5986128A (en) * | 1996-11-01 | 1999-11-16 | Monsanto Company | Use of monosodium iminodiacetic acid solutions in the preparation of N-phosphonomethyliminodiacetic acid |
| IES980552A2 (en) * | 1998-07-09 | 1999-08-11 | Agritech Chemical Ltd | Improved process for preparing N-phosphonomethyl iminodiacetic acid |
| WO2000014093A1 (fr) * | 1998-09-08 | 2000-03-16 | Hampshire Chemical Corp. | Synthese d'un acide phosphonomethyliminodiacetique au moyen d'un effluent reduit |
| AR029508A1 (es) * | 2000-04-14 | 2003-07-02 | Dow Agrosciences Llc | Proceso para remover y recuperar cloruro de sodio de los efluentes de desecho provenientes de los procesos de fabricacion del acido n-fosfometiliminodiacetico (pmida) |
| EP1283841B1 (fr) | 2000-05-22 | 2005-11-16 | Monsanto Technology LLC | Systemes de reaction pour preparer des composes de n-(phosphonomethyl)glycine |
| CN1200944C (zh) * | 2001-01-12 | 2005-05-11 | 巴斯福股份公司 | N－膦酰基甲基亚氨基二乙酸的制备方法 |
| US6641741B2 (en) | 2001-04-13 | 2003-11-04 | Dow Agrosciences Llc | Removal and recovery of chloride from phosphonomethyliminodiacetic acid process brine |
| TW200718706A (en) * | 2005-04-25 | 2007-05-16 | Monsanto Technology Llc | Altering the crystal size distribution of N-(phosphonomethyl)iminodiacetic acid for improved filtration and product quality |
| CN100436460C (zh) * | 2005-10-08 | 2008-11-26 | 重庆三峡英力化工有限公司 | 一种n-膦酰基甲基亚氨基二乙酸的合成方法 |
| CN100400543C (zh) * | 2006-09-08 | 2008-07-09 | 四川贝尔实业有限责任公司 | 亚氨基二乙腈水解制备双甘膦的方法 |
| CN101525350B (zh) * | 2009-04-22 | 2012-07-18 | 北京颖新泰康国际贸易有限公司 | 一种制备双甘膦的方法 |
| AU2010251897A1 (en) | 2009-05-28 | 2011-11-24 | Straitmark Holding Ag | Method for the manufacture of phosphonoalkyl iminodiacetic acids |
| CA2778858C (fr) | 2009-10-27 | 2021-01-12 | Straitmark Holding Ag | Procede de fabrication d'acide phosphonoalkyliminodiacetique |
| WO2012009860A1 (fr) * | 2010-07-23 | 2012-01-26 | 重庆紫光化工股份有限公司 | Procédé de synthèse d'acide n-phosphonométhyliminodiacétique |
| IN2015DN01080A (fr) | 2012-07-17 | 2015-06-26 | Straitmark Holding Ag | |
| CN104812765B (zh) | 2012-07-17 | 2017-06-06 | 斯特雷特马克控股股份公司 | 用于合成α‑氨基亚烷基膦酸的方法 |
| BR112015000990B1 (pt) | 2012-07-17 | 2020-04-28 | Monsanto Technology Llc | Método para a síntese de um ácido aminoalquilenofosfônico ouseus ésteres fosfatos |
| BR112015000988A2 (pt) | 2012-07-17 | 2017-06-27 | Straitmark Holding Ag | método para a síntese de ácido n-fosfonometiliminodiacético ou derivados do mesmo |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2609390A (en) * | 1950-06-01 | 1952-09-02 | Frederick C Bersworth | Phosphonic alkylene polyamino acids and method of producing same |
| US2895989A (en) * | 1956-06-22 | 1959-07-21 | Dow Chemical Co | Method for the preparation of iminodiacetic acid |
| CA775575A (en) * | 1961-11-13 | 1968-01-09 | R. Irani Riyad | Organic phosphorus compounds |
| GB1142294A (en) * | 1966-02-08 | 1969-02-05 | Albright & Wilson Mfg Ltd | Improvements in production of amino alkylene phosphonic acids |
| DE2021148A1 (de) * | 1970-04-30 | 1971-11-11 | Benckiser Gmbh Joh A | Verfahren und Anlage zur kontinuierlichen Herstellung von Aminoalkylenphosphonsaeuren |
| US3904668A (en) * | 1973-11-15 | 1975-09-09 | Grace W R & Co | Process for preparing iminodiacetonitrile and alkali metal iminodiacetates |
| SE7703448L (sv) * | 1976-03-29 | 1977-09-30 | Grace W R & Co | Forfarande for utvinning av glycin och iminodiettiksyra ur losningar innehallande natriumglycinat och dinatriumiminodiacetat |
| CH647528A5 (fr) * | 1978-10-27 | 1985-01-31 | Bcap Biolog Chem Act Pat | Procede pour la preparation de n-phosphonomethylglycine. |
| US4389349A (en) * | 1982-01-25 | 1983-06-21 | Cho Hung H | Process for preparing of N-phosphenomethyl glycine |
| US4657705A (en) * | 1985-09-23 | 1987-04-14 | Monsanto Company | Process for the preparation of N-substituted aminomethylphosphonic acids |
-
1984
- 1984-12-05 US US06/676,749 patent/US4724103A/en not_active Expired - Lifetime
-
1985
- 1985-02-25 ES ES540675A patent/ES8606367A1/es not_active Expired
- 1985-02-26 HU HU85711A patent/HUT39455A/hu unknown
- 1985-02-26 GB GB08504958A patent/GB2154589B/en not_active Expired
- 1985-02-26 AU AU39138/85A patent/AU568187B2/en not_active Expired
- 1985-02-26 CA CA000475168A patent/CA1240338A/fr not_active Expired
- 1985-02-26 DE DE8585870031T patent/DE3564688D1/de not_active Expired
- 1985-02-26 KR KR1019850001194A patent/KR870001766B1/ko not_active IP Right Cessation
- 1985-02-26 EP EP85870031A patent/EP0155926B1/fr not_active Expired
- 1985-02-27 BR BR8500859A patent/BR8500859A/pt not_active IP Right Cessation
- 1985-02-27 IL IL74454A patent/IL74454A/xx not_active IP Right Cessation
-
1986
- 1986-01-09 ES ES550748A patent/ES8703887A1/es not_active Expired
- 1986-01-09 ES ES550749A patent/ES8703888A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2154589A (en) | 1985-09-11 |
| AU3913885A (en) | 1985-09-05 |
| ES550749A0 (es) | 1987-03-01 |
| KR870001766B1 (ko) | 1987-10-06 |
| HUT39455A (en) | 1986-09-29 |
| BR8500859A (pt) | 1985-10-15 |
| IL74454A (en) | 1988-05-31 |
| EP0155926A1 (fr) | 1985-09-25 |
| DE3564688D1 (en) | 1988-10-06 |
| ES550748A0 (es) | 1987-03-01 |
| AU568187B2 (en) | 1987-12-17 |
| GB2154589B (en) | 1987-04-08 |
| GB8504958D0 (en) | 1985-03-27 |
| EP0155926B1 (fr) | 1988-08-31 |
| US4724103A (en) | 1988-02-09 |
| ES8703887A1 (es) | 1987-03-01 |
| ES8606367A1 (es) | 1986-04-16 |
| KR850007062A (ko) | 1985-10-30 |
| ES540675A0 (es) | 1986-04-16 |
| ES8703888A1 (es) | 1987-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20050809 |